57675-09-9Relevant academic research and scientific papers
Exploiting Alkylquinone Tautomerization for the Total Synthesis of Calothrixin A and B
Mori-Quiroz, Luis M.,Dekarske, Madeline M.,Prinkki, Austin B.,Clift, Michael D.
, p. 12257 - 12266 (2017)
The pentacyclic alkaloid calothrixin B (1) has been synthesized in 5 steps from murrayaquinone A (9). The key step involved the union of boryl aniline 31 with brominated murrayaquinone A (26). In this transformation, alkylquinone 26 undergoes tautomerization to a quinone methide, which is intercepted by boryl aniline 31 to forge a new C-N bond. An intramolecular Suzuki coupling, followed by dehydrogenative aromatization, completed the synthesis of calothrixin B. Subsequent N-oxidation of calothrixin B delivered calothrixin A. The successful synthesis of these alkaloids and the challenges that led to the development of the final synthesis plan are reported herein.
Synthesis of carbazoloquinone derivatives and their antileukemic activity via modulating cellular reactive oxygen species
Suematsu, Natsumi,Ninomiya, Masayuki,Sugiyama, Hodaka,Udagawa, Taro,Tanaka,Koketsu, Mamoru
, p. 2243 - 2247 (2019/07/03)
Carbazoloquinone alkaloids are of great interest as privileged structures for anticancer drug molecules. The purpose of this study was to investigate the structure-activity relationships of carbazoloquinone derivatives as anticancer agents. A series of ca
On-water reactivity and regioselectivity of quinones in C-N coupling with amines: Experimental and theoretical study
Martinez-Cifuentes, Maximiliano,Clavijo-Allancan, Graciela,Di Vaggio-Conejeros, Carolina,Weiss-Lopez, Boris,Araya-Maturana, Ramiro
, p. 217 - 224 (2014/03/21)
A study about the oxidative coupling of some representative carbo-and heterocyclic non-symmetrical quinones with aryl-and alkylamines, was carried out comparing dichloromethane and water as reaction mediums. We found that the on-water reactions gave better or, at worst, the same results as a conventional organic medium like dichloromethane. Descriptors derived from conceptual density functional theory and approaches of electrostatic nature, such as the molecular electrostatic potential, were used to explain the observed chemical reactivity and regioselectivity. Further, the on-water conditions were used to obtain 24 new aminoquinones with potential biological activity.
An in-water, on-water domino process for synthesis
Norcott, Philip,Spielman, Calan,McErlean, Christopher S. P.
supporting information; experimental part, p. 605 - 609 (2012/04/23)
An in-water, on-water domino process has been engineered as a green strategy for chemical synthesis. The process is driven by the different aqueous solubility of organic reactants and products, which are shuttled between the two phases of an emulsion. During this process, water serves as a reaction medium, a product partitioner and a reaction catalyst. The Royal Society of Chemistry 2012.
Green protocol for conjugate addition of amines to p-quinones accelerated by water
Yadav, Jhillu S.,Reddy, Basi V. Subba,Swamy, Tallapally,Shankar, Kattela Shiva
experimental part, p. 1317 - 1320 (2009/12/04)
Amines undergo smooth conjugate addition to p-quinones in H2O at ambient temperature in the absence of a catalyst to produce 2-aminoquinones in excellent yields. Significant rate acceleration of this reaction is observed in H2O compa
Structure-activity delineation of quinones related to the biologically active Calothrixin B
Bernardo, Paul H.,Chai, Christina L.L.,Guen, Maurice Le,Smith, Geoffrey D.,Waring, Paul
, p. 82 - 85 (2007/10/03)
Quinones such as Calothrixins A and B display a range of biological properties. As part of our ongoing studies to elucidate the mechanism of action of the Calothrixins, several related quinones were synthesized and tested for biological activity. The resu
Indoloquinones, part 8.1 palladium(II)-catalyzed total synthesis of murrayaquinone A, koeniginequinone A, and koeniginequinone B
Knoelker, Hans-Joachim,Reddy, Kethiri R.
, p. 1049 - 1052 (2007/10/03)
Regioselective addition of the appropriate arylamines to 2-methyl-1,4-benzoquinone followed by a palladium(II)-catalyzed oxidative cyclization opens up an efficient route to the naturally occurring 3-methylcarbazole-1,4-quinone alkaloids murrayaquinone A, koeniginequinone A, and koeniginequinone B.
Catalytic oxidative aromatic cyclizations with palladium
Akermark, Bjoern,Oslob, Johan D.,Heuschert, Ulrich
, p. 1325 - 1326 (2007/10/02)
Using tert-butyl hydroperoxide as oxidant, facile palladium-catalyzed cyclizations of arylaminoquinones have been performed.
